| YEAR | QUEEN | ATTENDANT | ATTENDANT | COMMENTS |
| 1935 | Chagrin Valley Home Week Association | |||
| 1936 | Ann Venchiarutti | Chagrin Valley Association | ||
| 1937 | Nellie Huggett | “Chagrin Valley Week, When It’s Blossom Time in the Valley” | ||
| 1938 | Viola Shelton-1st | Genevieve Eggleston-2nd | Jane Behlen-3rd | |
| 1939 | Jessie May Lommler | A Sequel to Blossom Time, “Harvest Time,” was held late in October, 1939 | ||
| 1940 | Carol Wass | |||
| 1941 | Eleanor Enslen | Janet Greed | Mary Lou Mercer | “Queen of Summer Time” in the Valley |
| 1942 | No Blossom Time Due to WWII | |||
| 1943 | No Blossom Time Due to WWII | |||
| 1944 | No Blossom Time Due to WWII | |||
| 1945 | Xenil Jefferson | Arline Miller-2nd | Carol Cruikshank-3rd | 1st Blossom Time After WWII |
| 1946 | ||||
| 1947 | ||||
| 1948 | Shirley Weber (Solon) | 4 Attendants – Beth Beattie was from Chagrin Falls | Blossom Time | |
| 1949 | ||||
| 1950 | ||||
| 1951 | ||||
| 1952 | ||||
| 1953 | ||||
| 1954 | ||||
| 1955 | ||||
| 1956 | Marilyn Post (Orange HS) | |||
| 1957 | Kaye Spielhaupter | Myrl Flynn | Susan Morton | |
| 1958 | Susan Morton | Holly Hurtt | Joan Schuster | |
| 1959 | Carol Nye | Shirley Grose | Loretta Rufener | |
| 1960 | Julie Maves | Karen Hurst | Marlaine Morse | |
| 1961 | Diana Campbell (KHS) | Trudy Sundstrom (OHS) | Samantha Epperson (CFHS) | |
| 1962 | Suzanne Sutton | Bonnie Jones | Candy Humiston | |
| 1963 | Susan Jamieson | Anne Lounsbury | Nancy Strick | |
| 1964 | Pam Peabody | Suzi Bartholomew | Sally Carpenter | |
| 1965 | Pamela Andberg | Leigh English | Janet Ismond | |
| 1966 | Ann Peabody | Reen McDermott | Marty Narten | |
| 1967 | Cheri Turner | Susana Indart | Joan Platek | |
| 1968 | Debi Karl | Cynthia King-Kenston HS | Sandy Hooder-Newbury HS | Barbara Grabner-Orange HS |
| 1969 | Cindy Thomas | Mary Ellen Doddridge | Roxanna Lyle | |
| 1970 | Nancy Anderson | Gretchen Hobart | Kathy Stevens | |
| 1971 | Debby Jackson | Carol Riethmiller | Beth Raymond | |
| 1972 | Cari Freemantle | Tina Langer | Holly Webster | |
| 1973 | Melanie Ingalls | Julie McDermott | Lori Bowser | |
| 1974 | Pam Fischley | Patti Lockert | Joan Brandon | |
| 1975 | Pam Houston | Gale Bamberger | Cynthia Carter | Gail Griswold |
| 1976 | Carol Jeffries | Linda Cross | Judy Bley | |
| 1977 | Eileen McDermott | Nena Peterson | Donna Phelps | |
| 1978 | Amy Jeffries | Kathleen McDermott | Sandy Seidel | |
| 1979 | Jeanette Borsh | Beth Cowhard | Candy Boblenz | |
| 1980 | Donna Edwards | Julie Green | Colleen Clegg | |
| 1981 | Betsy Sutcliffe | Jeannie Villo | Mary Kay Burke | |
| 1982 | Kendra Hopcraft | Lee Philpott | Jane Gluf | |
| 1983 | Robin Schlundt | Sally Bartunek | Sherry Kucera | |
| 1984 | Kristin Philpott | Alicia Burton | Deidre Bryan | |
| 1985 | Amy Brooks | Sarah Owen | Jane Mendelsohn | |
| 1986 | Natalie Gross | Kim Polomsky | Melissa Simko | |
| 1987 | Jamie Scolaro | Cindy Hopcraft | Lori Euritt | |
| 1988 | Carlene Cox | Halle Philpott | Lisa Kah | |
| 1989 | Vanessa Bello | Kristy Scolaro | Rachel Oler | Megan Thomas |
| 1990 | Megan Dustin | Ingrid Leusch | Alyson Schwartz | |
| 1991 | Megan Exline | Laura Wurster | Becky Buzogany | |
| 1992 | Tiggy Hopkins | Karis Gibbs | Meredith Mathe | |
| 1993 | Amy Exline | Christina Weisenbach | Kristen Worley | |
| 1994 | Jennifer Zierold | Jenny Stinson | Molly Lubs | |
| 1995 | Casey Abley | Cortney DeGross | Betsy Sutliff | |
| 1996 | Amy Spresser | Sarah Cooper | Meghan Gilkey | Dana Leary |
| 1997 | Elena Shaddow | Keri Hlavin | Mary Ellen Lee | |
| 1998 | Katie Sparger | Emily Smith | Barbara Lancaster | |
| 1999 | Alexis Wyszynski | Beth Clevenger | Ann DeRee | |
| 2000 | Theresa Collins | Rebecca Bloomfield | Elizabeth Arnold | |
| 2001 | Lizbeth Spresser | Ashley Torrey | Kim Patronite | |
| 2002 | Sara Grigera | Amy Booms | Julie Padavich | |
| 2003 | Abigail Blackburn | Marissa Patsey | Chloe Levien | |
| 2004 | Cassie Hart | Chelsea Bacher | Brittany Giordano | Kristen Schmittel |
| 2005 | Lindsay Rawot | Rachel Preyss | Elin Hudson | |
| 2006 | K.K. Carothers | Jessica Butler | Emily Metzger | |
| 2007 | Kate Sloan | Megan Devilliers | Ali Wisniewski | |
| 2008 | Trisha Burello | Liz Monda | Emily Yang | |
| 2009 | Erin O’Toole | Grace Fredrickson | Kate Yang | |
| 2010 | Maggie Clegg | Ariel Driecer | Emily Arjani | |
| 2011 | Brooke Chambers | Catherine Cashy | Jillian Ertel | Kathryn Mahoney |
| 2012 | Jen Andrews | Lizzy Biederman | Kathryn Aleksov | |
| 2013 | Katie Widman | Shannon Clegg | Rachel Clemens | |
| 2014 | Lily Manchester | Katie Ross | Kathryn Bullen | Payton Fricke |
| Haylee O’Hearn | Ellie O’Neil | |||
| 2015 | Avery Friedman | Lauren Mahoney | Jenna Hadbavny | |
| 2016 | Julia Bencko | Emily King | Caroline Hendricks | |
| 2017 | Molly Carroll | Milly Mason | Emily Owen | Bella McGreevy |
| 2018 | Maddie Miralia | Marley Vidmar | Anastasia Kotkovskaya | |
| 2019 | Catherine Coffey | Shannon Staley | Dinah Walter |